| 1 | Sat 5 Sep | 141-1 v Carshalton AthleticChertsey Town 1-1 Carshalton Athletic | Emirates FA Cup First Qualifying Round |
| 2 | Mon 7 Sep | 142-1 v Carshalton AthleticCarshalton Athletic 1-2 Chertsey Town | Emirates FA Cup First Qualifying Round Replay |
| 3 | Sat 19 Sep | 143-2 v AFC Greenwich BoroughChertsey Town 3-2 AFC Greenwich Borough | Emirates FA Cup Second Qualifying Round |
| 4 | Sat 3 Oct | 142-0 v Sheppey UnitedSheppey United 0-2 Chertsey Town | Emirates FA Cup Third Qualifying Round |
| 5 | Sat 17 Oct | 140-2 v Plymouth ParkwayPlymouth Parkway 2-0 Chertsey Town | Emirates FA Cup Fourth Qualifying Round |
| 6 | Sat 24 Oct | 144-0 v TakeleyTakeley 0-4 Chertsey Town | FA Trophy First Round |
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